Jove
Visualize
Contáctanos
JoVE
x logofacebook logolinkedin logoyoutube logo
ACERCA DE JoVE
Visión GeneralLiderazgoBlogCentro de Ayuda JoVE
AUTORES
Proceso de PublicaciónConsejo EditorialAlcance y PolíticasRevisión por ParesPreguntas FrecuentesEnviar
BIBLIOTECARIOS
TestimoniosSuscripcionesAccesoRecursosConsejo Asesor de BibliotecasPreguntas Frecuentes
INVESTIGACIÓN
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchivo
EDUCACIÓN
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualCentro de Recursos para ProfesoresSitio de Profesores
Términos y Condiciones de Uso
Política de Privacidad
Políticas

Videos de Conceptos Relacionados

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

10.3K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.3K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.7K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.7K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

3.9K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
3.9K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.7K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.7K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

6.0K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
6.0K
Preparation of Epoxides03:00

Preparation of Epoxides

7.9K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
7.9K

También podría leer

Artículos Relacionados

Artículos vinculados a este trabajo por autores compartidos, revista y gráfico de citas.

Ordenar por
Same author

Hydrazine-mediated carbonyl-alkyne/allene reductive olefination.

Nature communications·2026
Same author

Sequence Display enables large-scale sequence-activity datasets for rapid protein evolution.

Nature biotechnology·2026
Same author

One-Step-Three-Ring Propellanation Reaction of Yne-Vinylcyclobutanones Catalyzed by Nickel: Reaction Development, Mechanism, and Formal Synthesis of Modhephene.

Journal of the American Chemical Society·2026
Same author

Development and Mechanism of Rh-Catalyzed Keto-(5 + 1 + 2) Reaction of Keto-Vinylcyclopropanes and CO, and Answering Why Rh-Catalyzed Keto-(5 + 2) Reaction of Keto-Vinylcyclopropanes Fails.

Journal of the American Chemical Society·2026
Same author

Mechanistic Study of Cycloisomerization of 1,7-Allenenes and Guidance to Develop a [2 + 1 + 2] Reaction of 1,7-Allenenes with CO for Accessing <i>cis</i>- and <i>trans</i>-5/5 Skeletons.

Journal of the American Chemical Society·2026
Same author

Ynamide Protonation-Initiated N-Heteropolyene Cyclization.

The Journal of organic chemistry·2025

Video Experimental Relacionado

Updated: Aug 9, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

7.5K

Reacción controlada por liberación de deformación [4 + 2 + 1] de diene-enas cubiertas de ciclopropilo y monóxido de

Chen-Long Li1, Yusheng Yang1, Yi Zhou1

  • 1Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.

Journal of the American Chemical Society
|February 22, 2023
PubMed
Resumen
Este resumen es generado por máquina.

Las reacciones catalizadas por metales de transición ahora favorecen a los conductos de carga cíclica [4 + 2 + 1] sobre los productos [2 + 2 + 1] mediante el uso de dienos cubiertos de ciclopropilo. Este avance permite una síntesis eficiente de complejos esqueletos ciclicos y tricíclicos.

Más Videos Relacionados

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.1K
The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

12.2K

Videos de Experimentos Relacionados

Last Updated: Aug 9, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

7.5K
Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.1K
The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

12.2K

Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Metodología sintética

Sus antecedentes:

  • Las reacciones catalizadas por metales de transición de diene-ynes / dienes con monóxido de carbono (CO) generalmente producen conductos de carga cíclica cinéticamente favorecidos [2 + 2 + 1].
  • El logro de los conductos de carga cíclica [4 + 2 + 1] preferidos termodinámicamente en estas reacciones presenta un desafío sintético significativo.

Objetivo del estudio:

  • Desarrollar una nueva estrategia para la síntesis selectiva de [4 + 2 + 1] conductos ciclógenos a partir de diene-inas/dienes y CO.
  • Investigar el mecanismo por el cual se logra la regioselectividad deseada.

Principales métodos:

  • Utilizando como sustratos diene-inas y diene-enas cubiertas de ciclopropilo (CP).
  • Utilizando la catálisis de rodio (Rh) para la reacción de ciclización.
  • Haciendo cálculos químicos cuánticos para aclarar el mecanismo de la reacción.

Principales resultados:

  • La introducción de un límite de CP en la fracción de dieno dirige la reacción exclusivamente hacia los conductos de carga cíclica [4 + 2 + 1], suprimiendo la formación de productos [2 + 2 + 1].
  • La reacción demuestra un amplio alcance de sustrato, dando valiosas estructuras ciclicas de 5/7 que contienen una fracción CP.
  • El grupo CP en los conductos de carga cíclica sirve como un mango versátil para las transformaciones posteriores, permitiendo el acceso a diversos marcos cíclicos y tricíclicos.

Conclusiones:

  • La estrategia de dieno con límite de CP supera efectivamente el desafío de la regioselectividad en las adiciones cíclicas catalizadas por metales de transición [4 + 2 + 1] con CO.
  • La selectividad observada se atribuye a la liberación de tensión en el anillo dentro del grupo metilenociclopropilo (MCP) durante la reacción.
  • Esta metodología proporciona una ruta poderosa a las estructuras policíclicas complejas relevantes para la síntesis de productos naturales.